Insights

By Author: Sandra Stilwell

The Fashion Trials of an Island Girl

April is Gulfshore Life’s fashion month, so what better time to share insights into "fashion-on-the-run" from a busy Island Girl? For those of you who do not know me, eight of my businesses are on Captiva Island; one in Fort Myers. During the day, I’m running back and forth between my restaurants and board meetings at two universities, a not-for-profit and a bank. There are also community meetings on Sanibel and Captiva, as well as multiple off-island meetings.

My goal is to spend less time in meetings and more time fishing. I’m also busy with evening events. That means cocktail attire and evening gowns—lots of them. And don’t forget the themed costume events. Yes, I need a pretty diverse wardrobe. It’s divine now that I have a second home on the mainland. I no longer have to plan the full day’s attire ahead of time, and our island home doesn’t have to contain everything for every occasion.

That’s because island life is very relaxed and unencumbered. I just run around in our pink golf cart and wear flip-flops and sundresses or capris. If a man shows up in a suit and tie, he is immediately suspected of being an outsider. Likewise, ladies really can’t wear a business suit and expect to fit in. I’ve tried it. Islanders looked at me cross-eyed and asked, "What are you all dressed up for?" In any case, it was clear that I was overdressed.

To handle my on- and off-island fashion requirements, I’ve discovered the art of layering. Multifunctional skirts are a must. Off goes the jacket, and on goes a fun piece of island costume jewelry. I carry multiple shoes and clothes in my SUV. I’ve actually been known to run into a Taco Bell and throw on a gown for a black tie event. Hopping up and down while trying to get out of my sandals and into spiked heels—while not touching my bare feet to the floor—was the defining moment for me to seek help! It wasn’t pretty. Mix that with my next encounter, and I was sold on buying an off-island home.

One evening, i was driving home alone after midnight with my convertible top down. My music was blaring so I wouldn’t fall asleep on that secluded and lonely stretch near the J.N. Ding Darling National Wildlife Refuge. I rounded the curve and to my surprise, I had a very close encounter with an eight-foot alligator crossing San-Cap Road. As I slammed on the brakes, the gator’s mouth opened. My car slid sideways, screeching to a halt right next to the terrified gator. I was so petrified that I couldn’t scream. My little Porsche would have been no match for that gator. I definitely needed a base on the mainland.

If you think alligators are dangerous, they’re nothing compared to the disasters looming everywhere on the islands for shoe lovers. I love island life, don’t get me wrong. But no pair of Gucci heels is safe here. Designer heels are meant for paved parking lots, not the washed shell parking lots all over Captiva. They tear up your heels and trip you, and potholes form easily. Sometimes, when I’m in a rush, I decide to risk it. After all, I just need to stop by, sign a few checks, walk through a few of the restaurants, etc.

But even if you avoid the parking lots, there’s another danger lurking in wooden-decked walkways. We’re halted in our tracks when our spiked heels slip into the gaps between planks. The only way out of the mess is to take off our shoes and wiggle them out of their bondage. Here’s a tip: When you come to the island, wear sandals or flats. Bring your good shoes in your car and do a quick change just before walking into a restaurant.

The island is full of shops, art galleries and restaurants. We are all happy to see you and will welcome you. The diversity of the clothing shops is a very attractive part of shopping on the island. In Season, I try to get off island before the four o’clock traffic jam or wait until after six if at all possible. By planning your exit, you can save the extra half hour or so. When caught in traffic, you can do more shopping or stop by one of the local restaurants to pass the time until the traffic clears.

Southwest Florida is a bit of heaven. Sanibel and Captiva are our slices of island heaven. We live and breathe by our tourists and local residents bringing guests to the island. Please do come by and see us—just wear comfortable shoes.

I love island life, don’t get me wrong. But no pair of Gucci heels is safe here.